Milwaukee, Wisconsin
7/26
Photo: A view of Milwaukee, Wisconsin from St. Francis. (Photo via vjaksic / iStock / Getty Images Plus)
It's no secret that winter can be a bit harsh in Wisconsin, so it should come as no surprise that Milwaukee makes every moment of summer count. In addition to attending Summerfest, the Wisconsin State Fair, Brewers games and taking down cups & cones of frozen custard, locals head to their wealth of lakeside recreation spots and patio restaurants. Add to this the possibility of a long run by the Bucks in the NBA Playoffs and the fact the city will play host to the Democratic National Convention (July 13 - 16), and you have the makings of a summer for the ages.